How I run a Startup Weekend

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I’ve run a lot of Startup Weekends since I first got involved in 2010. I think I’ve facilitated over 60, but I lost count so let’s say 50. That means I’ve observed well over 100 other organizers and facilitators in action.

Once thing I’m sure of: everyone runs their Startup Weekend a little bit differently.

Like the other thousands of Startup Weekend volunteers out there, I have my own way of doing things. At every event I do, I run tiny experiments to learn which details truly affect the outcome. I’ve tested everything from the order of the facilitator slides to the way to arrange food on a table.

As it turns out, most things have zero impact on the success of the event.

So – beginners can take comfort in this truth:

It’s really hard to fuck up a Startup Weekend.

In its purest form, the format of a Startup Weekend is simple and beautiful and just works. Most of the decisions you will make as an organizer have to do with details that won’t jeopardize the outcome.

Because of this truth, when I run an event, these are my goals:

(1) simplify my life as an organizer

(2) maximize fun and learning for participants

(3) maximize fun and learning for the organizing team

As you read below, you might find that I do stuff you think is a waste of time, or that I don’t do something you think is critical. Keep an open mind, run your own experiments and decide for yourself. Maybe something I do won’t work in your local culture. Maybe I’m an idiot and you can convince me to change my terrible ways by leaving a comment.

I’m sharing this because (a) I’m curious if other experienced organizers and facilitators have reached the same conclusions, (b) I’m always looking to improve my approach and I hope this will start some conversations that lead to me changing my mind, and (c) it might save others – particularly beginners – some time and stress.

How I run Startup Weekends

A small number of exceptional coaches. We’ve all heard teams complain that coaches can be distracting. It’s a real problem, yet most of the Startup Weekends I go to have too many coaches. For an event with 75 attendees, I recruit 4 or 5 amazing coaches and ask them for 5-6 hours of their time. I find people that have experience coaching and are versed in Lean Startup methods. I meet with potential coaches before the event to make sure they’re gonna be great. I tell them that it’s their job to listen and ask the right questions, not impose their opinions. I find that fewer, higher quality coaches leads to a better experience for the teams – who get interrupted less and don’t have to explain themselves to 10 coaches – and a better experience for the coaches – who are able to dig in a bit deeper with teams, be more helpful, and stick around to see if teams take their advice.

I am an active coach. I do not separate myself from the event or huddle in “the organizers’ room.” As soon as teams form, I begin coaching. I find that in the first few hours together, I can make a big impact in helping teams decide what to focus on and how to communicate effectively. I question teams on their customer discovery activities. I help them write their customer interview scripts. I help them design experiments and analyze the results. I practice their pitches with them. My cell phone and laptop stay in my bag.

Three judges. More than five is too many. Less than three is not enough. Three is better than five. At five, the feedback is more high-level. At three it gets deeper and more helpful. Judges seem to have more fun themselves when it’s three rather than five.

I choose my judges carefully. Never ask people to be judges to win brownie points. Choose people that you genuinely believe will be good judges. Judges should be people that hear a lot of pitches. They should know the right questions to ask. Angel investors make great judges. GMs of accelerators. VC fund analysts. Not all serial entrepreneurs make good judges. The best judges know how to both encourage people but also push them on stuff that matters.

No speakers. Consider the following:

  • People don’t come to a Startup Weekend to see speakers. In fact, many people feel the allure of a Startup Weekend is that it doesn’t have speakers. Don’t forget Startup Weekend’s tag line: “No talk, all action.”
  • You don’t need a speaker to energize the room. That’s the facilitator’s job.
  • If you do want to have speakers, I’ve found that the best are past Startup Weekend winners giving advice on how to get the most out of the event (have them speak at the beginning), or an expert on a specific topic that’s helpful for the event like customer development or lean canvas (have them speak over lunch and make it optional).

I ask sponsors to participate. Great sponsors know that they’ll get more exposure and ROI by participating alongside attendees than they will from two minutes of stage time.

I run two workshops. One on customer discovery and empathy interviews (usually Friday night or Saturday morning) and one on experiments and prototyping (usually Saturday afternoon after teams have come back from their first round of interviews). I’ve found that just a little guidance in these two areas can drastically improve the final presentations.

I order extremely good food. I can’t stress how important it is to have good food. Here’a a conversation I’ve overheard many times: “How was that event you went to last weekend? What was it called, Startup Weekend?” Response: “It was great. I met some awesome people. And the food was amazing.” My point: People remember the food. Spend more money on food. Go local and healthy. And remember that carnivores can eat vegetarian food, so always over-order vegetarian options.

All teams working in one open floor plan space. I don’t let teams barricade themselves into a private room. One of the benefits of a Startup Weekend is being able to meet a lot of people in the community. Teams that hide in a room interact with fewer people. They also seem to have less fun.

This is leadership training for the organizers. As a facilitator, make sure your organizers are having a good time. Teach them everything you’re doing. Ask them to listen while you coach a team. Delegate stuff to them before they’re ready. Give them 100% of the credit. Your goal is to get them addicted to being an event organizer so they continue to help and get involved in other initiatives in the local startup community.

Ice cream social on Saturday night. And other fun surprises that attendees will tweet about and remember. Thanks to Fargo for this idea.

I work my ass off to get designers in the room. I have beef with designers. Not enough designers are entrepreneurs, and not enough of them participate in Startup Weekends. This calls for another blog post, but a lot has been written about this already.

Charge the same price for all three ticket types. I think if you charge non-technical participants more for a ticket, it signals that their skills are less valuable.

Pitch practice on Sunday. Assign a coach or do it yourself.

All organizing teams need to have:

  • At least 1 designer
  • At least 1 developer
  • At least 1 marketer
  • At least 1 female
  • At least 1 male
  • At least 1 student

A team of all developers is just as bad as a team of all marketers. A team of all women is just as bad as a team of all men. Diverse organizing teams lead to diverse attendees.

I ban surveys. Every time a team says “We did a Survey Monkey / Facebook Poll and 87% said they’d buy our product” a kitten dies. Surveys can be extremely misleading. They are for collecting quantitative facts only. Teams should be gathering qualitative data at a Startup Weekend. Teams should be trying to learn as much as they can about a problem that they think a specific type of customer has. The best way to do that is face-to-face empathy interviews and live experiments.

Don’t trust the Wi-Fi. Test it. Spend a few hundred dollars for additional wireless hotspots.

Lots of music, lots of energy. Link to awesome Spotify playlist.

Personal (not bulk) email reminders to all the VIPs. Send email reminders to coaches and judges the day before with the where/when details. Text them a few hours before. Don’t put them all on one email chain. Email each one individually. Treat them like celebrities. Have bottled water waiting for them in their seats.

I get my sleep. Get 8 hours of sleep every night. If you’re staying late both nights and coming in early both morning, you’re doing it wrong.

Always eat on Friday night with the attendees. Don’t find yourself shaking with low blood sugar at 11pm on Friday scaveging for whatever cold pizza is left

Stay hydrated. I drink 4 bottles of water every day during a Startup Weekend. I pee a lot, but I never get a headache.

That’s just some of the stuff I do that might be a little bit different from what you do. Like I said above, I’m always looking to improve my approach. If your experience tells you something different, please share so that I may learn and improve. Or if you do something unique, please share so that I can try it, too.

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